Entrepreneurial

As we all know, the life of an entrepreneur can be extremely hectic – so many great ideas, too little time and money to realize their full potential.

Yet how much of that time spent worrying about every little detail is truly constructive, or even necessary at all? The 3 a.m. conversation with yourself is one all entrepreneurs share, as they race through all the events of the day and panic about their exponentially expanding ‘to-do’ lists.

Dharmesh Shah, a self-proclaimed “professional geek,” who started his first company at 24 – Pyramid Digital Solutions, a 401(k)-plan software firm he self-financed with less than $10,000 and eventually sold for what Shah claims was “millions more” than the $15 million it turned in revenues in 2004 (the year before it was sold) – is the kind of entrepreneur whose brain is constantly running.

The sale allowed Shah to begin helping fellow entrepreneurs, by giving him the financial means to invest in early-stage technology companies in the Boston area, where he lives and co-founded Hubspot in 2006. Shah and Hubspot invented Website Grader, a free marketing tool which rates business sites based on marketing effectiveness and provides a score and useful advice on how to improve. It has garnered the company roughly $17 million in venture capital funds from General Catalyst and Matrix Partners since launching. Their intoxicating spinoff Twitter Grader (my account – twitter.com/jdcook – managed a ho-hum score of 72/100 with a ranking of 384,845 out of 1,878,414), has become one of the most-used Twitter apps.

In addition to his angel activities, Shah shares his knowledge on his blog site OnStartups.com.

One particularly useful post recounts one of those early-morning conversations Shah routinely experiences with someone he knows all too well – himself. It offers some sage advice for any entrepreneur thinking about or in the middle of running a startup. The post is titled: “Startup Conversations With Myself.”

If you’re a more visual person and have five minutes to spare, you can watch Shah’s YouTube video on what Hubspot is all about.